The Journal of Organic Chemistry

Regioselective alkylation of anthrahydroquinone and anthrone in water with quinonemethides and other alkylating agents

DR Dimmel, D Shepard

Index: Dimmel, Donald R.; Shepard, Donaline Journal of Organic Chemistry, 1982 , vol. 47, # 1 p. 22 - 29

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Citation Number: 33

Abstract

Anthrahydroquinone (AHQ) and anthrone are alkylated in the Clo position by quinonemethides, generated in situ from p-acetoxybenzyl chlorides, to give adducts 13-15, 24, 25, 28, 29, and 32. Aqueous alkylations of AHQ with methyl vinyl ketone, cinnamaldehyde, and benzyl chloride also produces Clo-substituted 10-hydroxyanthrones. Simple ketones and aldehydes do not, however, alkylate AHQ in aqueous alkali.